Sodium Bicarbonate → N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-4-hydroxybutanoyl)-3-fluorophenyl)pyridine-2-carboxamide

HRID 13383

반응식

HRID 13383 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])=[CH:9][C:8]=1[F:22].[Si:23]([O:30][CH:31]1[CH2:35][CH2:34][O:33][C:32]1=[O:36])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>O1CCCC1>[Si:23]([O:30][CH:31]([CH2:35][CH2:34][OH:33])[C:32]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])=[CH:9][C:8]=1[F:22])=[O:36])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 50462413-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-oneHCID 23145244N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 67482856N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-4-hydroxybutanoyl)-3-fluorophenyl)pyridine-2-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3.1 ml of n-butyl lithium (2.66 M hexane solution) was dropwise added to a tetrahydrofuran (100 ml) solution of 1.1 g of N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamide at −78° C., and the reaction liquid was stirred at the same temperature for 15 minutes. 1.21 g of 3-((t-butyl(dimethyl)silyl)oxy)dihydrofuran-2 (3H)-one was added to the reaction liquid, and the reaction liquid was stirred at the same temperature for 1 hour. Aqueous saturated sodium bicarbonate solution was added to the reaction liquid at the same temperature, then heated up to room temperature and extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1) to obtain the entitled compound as a colorless oily substance.

후처리

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred at the same temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
  8. customto obtain the entitled compound as a colorless oily substance

출처 및 근거

ORD 기록
ord-5792d20b11a24431869bed1f57a12458
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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